


In Your Hands Now

by keefling



Series: Playdates [4]
Category: Critical Role (Web Series)
Genre: Aftercare, Dirty Talk, Dom/sub, Established Relationship, M/M, Masturbation, Relationship Negotiation, Riding, Risk Aware Consensual Kink, Safeword Use, Trans Male Character, Vaginal Sex, Verbal Restraints
Language: English
Status: Completed
Published: 2018-07-03
Updated: 2018-07-03
Packaged: 2019-06-04 17:06:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,051
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15151736
Author URL: https://archiveofourown.org/users/keefling/pseuds/keefling
Summary: “I want to know what it feels like,” said Molly, touching his forehead to Caleb’s. “You know, what I do to you.”





	In Your Hands Now

**Author's Note:**

> I love this ship. I have never loved anything so much. I would die for them.
> 
> I recommend reading the rest of the _Playdates_ series first for additional context. 
> 
> Caleb is a trans man in this fic and I use feminine-coded words to describe his genitals.

Mollymauk was exhausted.  Not sleepy or tired, but emotionally exhausted.  Although he made his best effort to put on a smile for the rest of the group, thoughts of the past, present and future tumbled through his mind too quickly to entertain a single one.  While Molly was not prone to bouts of anxiety, he felt claustrophobic in his own head.  The humid air did not help; the weather had been relentlessly hot for days and Molly was finding it hard to breathe. 

He wished he could have spent just one more hour with Caleb in their room before hitting the road.  Molly occupied himself with thoughts of Caleb, who piled into the cart with the others while Molly rode on horseback alongside Fjord.  He smiled, recalling the first time Caleb had kissed him on the mouth in front of everyone at breakfast so that he could steal a slab of ham from Molly’s plate.  The party had whistled and hollered and their respective roommates exchanged knowing glances from across the table.  Caleb had buried his blushing face in Molly’s shoulder but when the commotion died down, he had been smiling.  Caleb was comfortable.  Caleb was happy.  Caleb was eating. 

Being on the move was nothing new for Molly, in fact he had never settled down anywhere for more than one week at a time, but not being allowed alone time with Caleb was making him restless.  He missed the foundation on which they had built boundaries and the sense of purpose he felt when he was in control.  The sex was great, but it was secondary to the emotional comfort that was established in their sessions.  He needed someone to be his anchor, and Caleb was the only person who could. 

A couple days later found the party in a small town that was not marked on their map.  The sun had already set in the west, taking the humidity with it.  Molly longed to take Caleb to bed and he made it evident by casting him smoldering looks and licking his lips far too often, eventually receiving a glare back that said,  _ not yet. _  So Molly was patient, ate dinner with the party and entertained their conversation until they agreed to retire. 

When Caleb shut the door to their room behind them, he barely had time to light the bedside lamp before Molly pounced.  He pinned Caleb to the door and kissed him hard.  Caleb made a surprised noise in the back of his throat, but he grabbed Molly’s shoulders to hold him in place while he kissed back.  Molly’s lips traveled down Caleb’s neck, carelessly sucking hard enough to leave bruises. 

“Molly!” Caleb gasped, digging his fingers into Molly’s shoulders.  “Slow down, please.” 

Molly pulled back, flushed and panting.  “I’m sorry,” he said.  “I should have—”

“Shh, shh,” Caleb cut him off.  He brushed a curly lock of hair out of Molly’s face and cupped Molly’s cheek, looking at the tiefling with eyes soft and full of understanding.  “You need something.” It was not a question. 

“I want to know what it feels like,” Molly said, touching his forehead to Caleb’s.  “You know, what I do to you.” 

Caleb sucked in a breath.  Molly watched his face for a reaction, but he could read nothing past the slightly furrowed brow.  Caleb placed a hand on Molly’s chest and walked him backwards until he was trapped between Caleb and the bed. 

“And that is how you ask for things?” Caleb chided.  The familiar words Molly had once spoken to Caleb left Caleb’s mouth and went straight to Molly’s dick.  Molly felt shame prickle over the back of his neck, followed by the warmth of arousal that spread outwards from his belly.  He looked down, unable to keep Caleb’s gaze. 

“No,” Caleb said, lifting Molly’s chin up with a finger.  “You will look at me.  Tell me what you need.” 

“I need you to take control of me tonight,” Molly said.  “I don’t want to think.  I just want to please you, my love.” 

Caleb pressed a chaste kiss to Molly’s lips.  “Thank you, Mollymauk.”

Molly’s heart swelled with gratitude for the man before him.  He had never asked this of anyone before, not even a casual partner.  Caleb was the first and only person he trusted with his entire being, mind, body and soul. 

“I want you to strip, then I want you to lie down on the bed and close your eyes.  Can you do that for me,  _ liebling? _ ”

“Absolutely,” Molly answered, already wriggling out of his coat. 

“Good,” Caleb said, stepping back to give Molly space. 

Molly untucked his shirt and lifted it over his head, trapping his arms in the fabric as he folded them behind his neck.  He arched his back and stood on tiptoe, swaying his hips and baring his nude torso to Caleb, whose eyes were fixed somewhere around Molly’s belly button. 

“Like what you see, hmm?” Molly teased, watching Caleb’s face redden.  He threw his shirt to the side and smoothed his hands down his body, resting them on his hips. 

“ _ Ja, _ very much,” Caleb said, nodding eagerly.  He had taken off his coat and book holsters and clasped his hands behind his back, presumably to keep from fiddling with his fingers or pieces of clothing.  Caleb frowned when Molly toed off his boots and kicked them away; Molly knew he was a fan of those boots, but Molly had not been instructed to keep them on, so off they went. 

Molly let his belt fall and pulled the drawstring on his trousers, hooking his thumbs under his waistband.  Caleb failed to suppress a quiet moan when Molly exposed his angular hips, and Molly failed to keep himself from grinning.  Molly knew he was hot.  He knew Caleb thought he was hot.  He liked being on the same page. 

Molly finally let his trousers and underclothes fall to the floor and stood, fully nude, in front of Caleb.  His soft cock rested at ease between his legs, but from the fiery look in Caleb’s eyes as he raked his gaze down Molly’s body, it would not stay that way for long. 

A moment of silence passed before Molly remembered the second half of his instructions.  He sat on the bed and scooted back until his head rested on the pillow, closed his eyes and waited for Caleb’s approval.  He listened to the shuffling that could only be Caleb shedding his clothes, then felt the bed shift and dip in four points around him. 

“Open your eyes,” Caleb said, and when he did, Molly inhaled sharply. 

Caleb loomed over Moly, naked, framing him on hands and knees.  But what caught Molly’s breath was Caleb’s hair, tied back into a tight, messy ponytail.  Caleb smiled down with his blue eyes unobscured.  Molly reached a trembling hand out to brush a loose strand of hair behind Caleb’s ear, casing Caleb to blush and look away. 

“Mollymauk,” he said, uncertainly.  “I....I do not know what I am supposed to do now.” 

Molly chuckled and wrapped his arms around Caleb’s waist.  Caleb giggled along nervously and let Molly pull him into a sitting position on his thighs with Caleb’s knees on either side of Molly’s hips. 

“Think about what you want to do to me,” Molly suggestion, smoothing his thumbs over Caleb’s hip bones.  “Or, what you want me to do  _ for _ you.  Just relax and do what comes naturally, love.  I will follow your lead wherever you take me.” 

Caleb nodded.  “Is anything off-limits?” 

“I don’t want to be physically restrained tonight, or blindfolded—I want to see you.”

“Do you have a safeword?”

“Scimitar,” Molly said, skimming the first word from the top of his head.  “And yours?”

“I don’t need—” Caleb tried to argue. 

“Caleb,” Molly cut him off.  There would be no lapses in safety. 

“Bugbear.” 

“Thank you, love.  Continue?” 

“Alright,” Caleb said, the air of authority returning to his voice.  “Grab onto the headboard.  Do not move your hands.”

Molly lifted his hands above his head and grabbed hold.  He shook the frame a little, testing the sturdiness of the wooden structure. 

“Good boy,” Caleb said, and Molly’s cock stirred.  The endearment by which he had called Caleb by dozens of times dripped from Caleb’s lips like sweet molasses, thickened by his accent, and Molly wanted to savor every drop. 

Caleb arched over Molly and dragged his hands over Molly’s chest.  He pinched his nipples, making Molly gasp and squirm, but Caleb’s hands were gone as quickly as they came.  He straightened himself, tipped his head back and, with a soft moan, teased his fingertips over the sensitive insides of his own thighs, through the sparse hairs that dusted his skin. 

“Watch me,” Caleb breathed, as if Molly’s eyes were not already fixed on the most breathtaking sight in the room.  Caleb’s eyelids fluttered closed and he sucked an index finger into his mouth, swirling his tongue around it and wetting it sufficiently.  He reached between his legs, past the trail of reddish hair that grew thicker the farther down it went.  He put two fingers on either side of his clit and pressed down, making it pop out from between his lips.  Molly did not blink when Caleb began rubbing his clit in slow circles with the tip of his finger. 

“Ah, ah, Molly,” Caleb moaned, sending shivers down Molly’s spine.  Molly whined in response; watching Caleb touch himself while Molly’s cock remained neglected right in front of him was torture. 

Caleb dipped his fingers between his slit and Molly could hear them sliding through his slick entrance when he slipped them inside.  He added a third finger and moved them in and out, gaining speed and panting through parted lips.  Every part of it was ridiculously hot—his flushed chest, his hair pulled back, the way his eyes rolled back when he added a fourth finger.  Molly’s cock bobbed between his legs, hardening at the sight of Caleb, beautiful and shameless. 

Caleb suddenly pulled his fingers out with a shaky sigh.  He put two soiled fingers to Molly’s lips which Molly eagerly took inside.  He sucked them in to the second digit, inhaling the musky scent while he lapped the salty cum from Caleb’s fingers.  When he took them away, Molly chased his hand, darting his tongue out for one last taste of his fingertips. 

“Mmm, Mollymauk,” Caleb purred, deliberately wiping his wet fingers on Molly’s bare chest.  “You are being so good for me, but let me see if you can keep your hands to yourself when I fuck myself on your cock.  You will be still until I cum, understood?”

“Yes, Caleb,” Molly said, still gripping the headboard.  “Understood.” 

Caleb leaned down for a quick kiss, lasting only for a heartbeat.  Molly was greedy. He wanted more, but he was grateful for whatever Caleb was willing to give him.  He would be good for Caleb.  He would be patient, and Caleb would reward him for it because Caleb was kind. 

Caleb shuffled forward on his knees and hovered above Molly’s dick.  He dropped his weight and ground down, pulling a soft cry from Molly.  Planting both hands on either side of Molly’s chest, Caleb began rocking forwards, dragging Molly’s cock through his dripping slit.  Both were panting hard after only a few moments of friction.  Molly’s composure was fading fast; he was unused to restrictions, and not being able to touch when and where he wanted was driving him mad. 

“Fuck, Caleb, you’re gorgeous,” Molly murmured, watching Caleb’s muscles flex as he humped Molly’s cock.  The low light cast dramatic shadows across his naked body, making him look more like a work of art than a man.  Caleb had a look of absolute determination on his face; his teeth gritted and his brow furrowed in concentration. 

“Your cock feels so good, Mollymauk,” Caleb sighed, slowing his hips and coming to a rest with Molly’s dick tucked snugly between his legs.  “I could do this all night.” 

“Oh, Caleb, you know I would let you,” Molly said, hoping Caleb could feel his cock throbbing against his clit. 

“But I want you inside me so badly,” Caleb said.  “Do you want that, Molly? Do you want me to ride your cock?” 

“Oh, gods, yes, Caleb, yes!” Molly cried, his tail thrashing against the bed behind Caleb.  “Please, take me any way you want me.  Please, darling, I’m yours.” 

“I like it when you beg,” Caleb said, amused.  He took Molly’s dick in both hands and slowly twisted his fists around it, lubricating Molly’s length with his own slick cum.  “I’m ready for you, Molly.  Are you ready for me?” 

“Yes, Caleb, please, Caleb, fuck me, fuck me,  _ please— _ ” the words poured incoherently from Molly’s mouth.  If he was in his right mind, even Molly might have been embarrassed by his lack of self-control.  But giving up control was the reason he was there, pinned beneath Caleb and babbling nonsensical pleas into the heavy air.  He was safe with Caleb, free of judgment and expectations.  The moment he broke down the wall of the careful composure he built around himself felt like he was being pulled from the earth again, the suffocating soil crumbling away and the taste of fresh air on his tongue, filling his lungs for the first time.  It had been too long since Molly felt truly, genuinely free. 

Caleb rose to his knees and guided Molly’s cock head inside of him, both of them moaning together when the tip popped inside. 

“Alright, Caleb?” Molly asked when Caleb did not move.  He trembled in place with one hand still wrapped around Molly’s dick, hissing through clenched teeth. 

“Ohh, give me a moment,  _ ja? _ ” Caleb laughed airily.  “You are quite big.” 

Molly beamed at the mention of his girth, and nodded.  “Take all the time you need, dear,” he said, and although he was dying to be inside Caleb, he meant it. 

Caleb steadied himself with one hand on Molly’s chest and, after a series of deep breaths, sank down onto Molly’s cock.  Molly threw his head back; the sensation of Caleb’s cunt clenched tight around him was dimming his vision with every squeeze of his inner walls. 

“Comfortable, love?” Molly asked when the room stopped spinning. 

“Mm, _ ja, _ very comfortable,” Caleb answered.  He arched his back, baring his chest and throat for Molly to see but not touch.  “I know you like it when I keep your cock warm inside of me, but tell me how you like this.” 

Before Molly could ask,  _ like what?   _ Caleb pulled himself almost completely off Molly’s cock and slid back down, tantalizingly slow, drawing a gasp from Molly and a warm chuckle from Caleb.  He did it again, and again, until Molly’s dick was rhythmically pumping in and out of him. 

“Mmm, I like this quite a bit, darling,” Molly purred, and while he was enjoying the friction, he enjoyed watching Caleb even more.  When Caleb had first come to Molly, he had not removed a single item of clothing, and now he was riding Molly’s cock like it was his birthright. 

“Oh, fuck, Molly, I’m close,” Caleb gasped, much sooner than Molly had anticipated. 

“Already, dear?  You don’t last long,” he teased.  He grinned up at Caleb, baring his teeth. 

“Do not be a brat, Mollymauk,” Caleb scolded.  “Remember that I decide when you can cum.” 

The ragged breathing took the edge off Caleb’s threat, but Molly took the words to heart.  “I am at your mercy, Mr. Widogast,” he said. 

“Good boy,” Caleb said, patting Molly’s cheek.  Sweat dripped down his brow and his messy ponytail was coming undone from the force of his bobbing head while slamming his hips down, thoroughly fucking himself on Molly’s erection. 

“Cumming, ahh, I’m cumming, Molly!” Caleb cried.  His knees gave out with Molly’s cock buried inside of him.  Caleb’s shoulders shook, his thighs trembled, and the muscles in his cunt rhythmically contracted around Molly’s dick.  He tried to swallow the noises he made, but several choked-out, high-pitched whimpers sounded in his throat. 

When Caleb lifted himself off Molly with a wet sound, Molly felt a hot flood of cum pour over his dick and balls, down his ass crack and onto the bed. 

“Fuck,” Molly breathed.  “That’s so hot.” 

Caleb grinned wide, and in combination with his hungry eyes and wild hair that clung to his sticky forehead, the man looked crazed.  Molly was shocked silent when Caleb lined up Molly’s dick with his entrance and sank down on it again, ready for round two.  Caleb had acclimated to the length and was already panting heavily as he bounced up and down, losing himself in the pleasure that he found with the pointed tip hitting that sweet spot deep inside of him.  Molly could feel his own orgasm simmering in his abdomen.  His eyes fell closed as he began to chase it, flexing his thighs while he did so. 

“Do you want to cum, Mollymauk?” Caleb asked.  He slowed his movements and began massaging his clit, large and red and swollen. 

“Oh, fuck, Caleb, fuck yes, please, let me cum,” Molly pleaded, even more desperate than the first time he had begged.  Not only was he aching for release, his arms were getting sore from where they were held above his head. 

“You will come inside of me, Molly.” 

Caleb’s words sent a surge of excitement down to Molly’s balls, and Molly grinned.  “Gladly, if that’s what you want, my dear.” 

Caleb laughed.  He leaned over and tapped Molly on the nose.  “I was not asking, Mollymauk.  Now, cum with me.” 

Caleb barely moved at all before Molly’s orgasm crested from Caleb’s command alone, still gripping the headboard until his fingers went numb.  He thrashed around like a chained animal, bucking his hips up into Caleb’s tight heat.  His mind blanked out from the force of his orgasm, and when he came to, he was whimpering through gritted teeth with tears streaming down his cheeks. 

Caleb rolled his hips in a circle, squeezing Molly’s cock as Molly continued spilling inside of him.  Caleb reached behind himself to squeeze Molly’s balls as he milked him for every last drop of cum Molly had to offer.  Without warning, Caleb pulled off Molly with a shout, vigorously rubbing his clit while he lifted his hips and squirted Molly in the chest as he came.  It trickled down the sides, tickling Molly’s ribs and pooling in his belly button. 

“Holy shit,” Molly gasped, wide-eyed.  “Gods, you’re amazing.  I didn’t know you could do that, love.” 

“I did not know that I could do that, either,” Caleb said, laughing in disbelief.  His laughter quickly turned to sobbing in great, strenuous heaves that shook his shoulders and hollowed his chest.  Caleb suddenly pitched forward, falling to his elbows and trembling against Molly’s chest while their combined cum dribbled down his thighs. 

“Oh, darling, my darling Caleb,” Molly cooed, wanting Caleb to know he was still there in the midst of the highly stressful reaction Caleb was having.  Caleb sobbed and rested his forehead on Moly’s shoulder, panting heavily against his sweaty skin.  Molly turned to nuzzle Caleb’s cheek, wishing he could touch him, hold him, stroke his hair, but Caleb had not given him permission do so.  Caleb did not move or return Molly’s affection.  He was obviously shaken. 

“Bug….bugbear,” Caleb whimpered, exercising his safeword for the first time.  “Please, will you hold me? Just for a moment?” 

“Of course I will,” Molly said.  “Come here, my love.” He let go of the headboard and, ignoring the pins and needles in his hands, wrapped his arms around Caleb’s shoulders.  Caleb collapsed onto Molly’s chest, ignoring the mess he had made between them.  Molly tugged what was left of his tied back hair down from its ponytail and ran his fingers through it, combing his wild locks back into place. 

“I am…..I’m sorry,” Caleb whined after his breathing slowed. 

“Shh, don’t be sorry,” Molly murmured.  “This is why we have safewords, to use them when we need to.”  With one arm still clutching Caleb to his chest, Molly reached blindly over the side of the bed and fished around in his pile of clothes for a waterskin he knew was half-full.  He popped the cork with his teeth and pressed it to Caleb’s lips.  “Drink, please.” 

Caleb rolled onto his side and took the waterskin, drinking deeply until it was empty.  He dropped it on the bed and tucked his head under Molly’s chin. 

“How are you feeling?” Molly asked after a few moments of silence. 

“Overwhelmed,” Caleb said.  “Overstimulated.  I….I have never come so hard in my life.  I was not ready for it.”

Molly laughed warmly.  “It was quite the performance.  You are a very talented man, Caleb Widogast.” 

Caleb snorted, his breath tickling Molly’s skin.  “That means a lot, coming from you.” 

“Perhaps you have a future in this sort of, ah, entertainment,” Molly teased. 

Caleb giggled and Molly could feel the bubbly laughter against his chest.  “ _ Nein, _ this is for you, Molly.  Only for you.”

“Mmm, I like that even better,” Molly said, a lightweight possessiveness curling in his chest, “Only for me.” 

“I love you, Molly,” Caleb murmured, pressing his whole body against Molly’s side.  “But you have taken so much out of me, I do not think I can continue.” 

“Continue?  Gods, Caleb, you’ve given more than enough.  I feel incredible.  I feel light, like my head’s been cleaned out.  Is this what it feels like? When I do it to you?” 

“ _ Ja,  _ well, yes, I think so,” Caleb said.  “I do not have to think when you are in control.  It is a blessing.” 

“Likewise,” Molly agreed.  “I think I want you in control more often, if you don’t mind.  Did you enjoy it, love?” 

“Yes, I did,” Caleb said.  “I loved having you writhing beneath me.  You are very attractive, but I have never been more turned on than when you were begging me to let you cum.” 

“It’s settled then,” Molly decided.  “We’ll take turns depending on what our needs are.”

“That sounds wonderful,” Caleb sighed.  He nudged Molly’s chin with his nose and Molly turned his head to kiss him.  The kiss was tender, their lips moved slow and their tongues only touched in passing.  Molly sighed against his lips, full to the brim with gratitude for the man beside him.  Caleb eventually dropped his head onto Molly’s shoulder, his body weak with sleepiness. 

“Sweetheart,” Molly tried, gently jostling Caleb’s shoulders.  “The bed’s ruined.  Can you get up, love?”

“No,” Caleb mumbled. 

“If you don’t get up, I’ll have to carry you.”

Caleb grunted in protest but did not move. 

“Alright then, up we go.”  Molly gathered Caleb in his arms, one supporting his back and the other below his knees.  He carried him the short distance to the other bed in the room and laid him down gently. 

“Gods, we’re a mess.  I’m going to get you a cloth,” Molly said.  “I’ll be right back.” 

After wiping down his own chest and cock, Molly took a warm, damp cloth to Caleb’s groin and thighs.  He could do nothing for the soiled bed, but that was easily forgotten. 

Molly put out the lamp and crawled into bed behind Caleb, who had rolled onto his side.  He molded himself to the contour of Caleb’s body and sighed happily against the back of his neck. 

“I love you, Caleb,” Molly said, but Caleb was already asleep.  He would say it again when Caleb woke up, and infinitely more times after that, because that is what was in his heart, and that was what Caleb deserved to hear. 

Molly lied awake for a while, but not from restlessness.  He wanted to bask in the moment for as long as possible before sleep took him.  He would take care of Caleb, and could rest easy knowing that Caleb would take care of him.  Molly had known what love was, objectively at least.  He had said he understood it and was simply uninterested in commitment, but he had never considered that Caleb had already given him what love had to offer. 

**Author's Note:**

> Well here we are folks! This is the last *planned* story in the _Playdates_ series but that doesn't mean I won't continue. Thank you all so much for your comments, kudos and encouragement!


End file.
